Benzyl Alcohol → HCID 19711369, compound

Participants

Reaction Steps

A solution of t-butyl 3-[3-(2-carboxy-1-propyl)-5-(3-pyridylmethyl)phenyl]propanoate (Preparation 38; 1.84 g), diphenylphosphoryl azide (1.45 g) and triethylamine (0.53 g) in dry 1,4-dioxane (12 ml) was heated at 100° C. for 45 minutes. Benzyl alcohol (0.78 g) was then added and the resulting solution heated under reflux for 18 hours and then evaporated under vacuum. The residue was chromatographed on silica gel using dichloromethane:methanol (95:5) as eluent, then the product fractions combined and evaporated under vacuum to give the title compound as an oil (2.30 g); Rf 0.25 (SS 1); δ (CDCl3): 1.08(3H,d), 1.40(9H,s), 2.48(2H,t), 2.55-2.63(2H,m), 2.81(2H,t), 2.89(2H,s), 3.89-3.95(1H,m), 5.07(2H,s), 6.82(1H,s), 6.87(2H,s), 7.12-7.18(1H,m), 7.27-7.42(6H,m), 8.40- 8.45(2H,m).

Provenance & Evidence